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Issue 11, 2016
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Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions

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Abstract

Chiral scaffolds of 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane were used for the construction of new modular catalysts containing complexing moieties pyridine, 2,2′-bipyridine and 1,10-phenanthroline appended by an imine linkage. The coordination abilities of the new ligands towards Zn(II) were investigated using NMR and UV spectroscopy. The plausible structures of the [ZnL2]2+ and [ZnLXn](2−n)+ complexes formed were established by comparison of the experimental and DFT-calculated NMR spectra. The catalytic application of the [ZnLXn](2−n)+-type complexes in the asymmetric aldol reaction of ketones with aromatic aldehydes produced an excess of the respective syn-aldols in up to >98% ee.

Graphical abstract: Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions

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Publication details

The article was received on 19 Jul 2016, accepted on 30 Sep 2016 and first published on 30 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ02251K
Citation: New J. Chem., 2016,40, 9795-9805
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    Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions

    E. Wojaczyńska, J. Skarżewski, Ł. Sidorowicz, R. Wieczorek and J. Wojaczyński, New J. Chem., 2016, 40, 9795
    DOI: 10.1039/C6NJ02251K

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